Long before Jeff Clark was surfing Mavericks by himself and Laird Hamilton was conquering skyscraper-high waves, San Diego had its own big wave pioneer. His name was Allen “Dempsey” Holder, a lifeguard who was stationed at the end of Palm Avenue in Imperial Beach.

Holder in the late 1930s was the first to surf the Tijuana Sloughs, the premiere big wave winter spot in the continental U.S. Eventually, other surfers would test their manhood at the Sloughs as well.

Compared to San Diego’s surfing pioneers, many modern-day surfers have cajones the size of marbles. It’s staggering to imagine the conditions Holder and his big-wave brethren braved: water temperature in the low 50s, no wetsuits or leashes, getting past the break with boards heavier than Olympic barbells, long swims to shore (the Sloughs is a far offshore break), and riding 20 foot faces.

These were true watermen. More accurately, they were waterboys. Many of these surf pioneers were teenagers when they first started surfing the winter swells of the 1930s and 40s. Like any fisherman telling a hyperbolic yarn, maybe some of the stories that San Diego’s first surfers tell are slightly exaggerated, yet there’s no doubt that they were fearless aqua-blazers with few cares in the world other than waiting for the next swell.

To this day, this first generation of modern-era surfers have photographic memories of what their first boards looked like, the exact dimensions to the eighth-inch and the materials used to shape them. They also remember the proportions of their friends’ boards.

Imagine surfing Sunset Cliffs, PB point and Windansea, enjoying these epic breaks all to yourself with just a few of your friends. Not a care in the world. You didn ‘t even have to carry your board home; you could just leave it right on the beach. Nobody would steal it because it was too heavy. Also imagine having bonfires and parties on the beach. Can’t do that anymore…you so much as pull out a lighter on the beach and you might get fined.

Big-wave TJ Sloughs legend Dempsey Holder is deceased as is Charlie Wright, who legend has it, might have been the first person to surf in San Diego. Several San Diego surfing pioneers are still alive and eager to relive their days of surfing epic swells with no lineups.

It’s believed that the Hawaiian surfing ambassador and Olympic swimmer Duke Kahanamoku instructed Wright, who lifeguarded and lived in Old Mission Beach , how to construct a pine and fir surfboard. Wright enjoyed tandem surfing with Faye Fraser (also deceased). The California Surf Museum in Oceanside has a picture of the two in tandem action.

Perhaps the oldest living surfing pioneer is Emil Sigler, who is 94 and lives in Normal Heights. Although home bound in a chair for most of the day, Sigler still seems tough as nails. From his living room off of Adams Avenue, Sigler, who only has one good eye, tells fascinating stories.

“I arrived in 1928 from San Francisco,” says Sigler. “I was 18 at the time. One day I was a couple blocks south of the Old Mission Beach lifeguard tower. I saw a couple of 10-foot long black boards laying up on the sea wall. They were made with two pieces of wood, each three inches thick by 12, with two bolts and a sealed cap over the top, and shaped with a slight vee bottom. I found out they belonged to Charlie Wright. I asked him if I could use it and he said, ‘Sure, go ahead, help yourself.’

“I told Charlie that I’d put it right back where I found it. The board was too heavy for me to handle at first, so I went straight in on small waves. That was my first connection with a surf board. The first couple times I tried to surf I thought the board was going to hit me in the head and kill me.”

Sigler eventually focused his pursuits as a lifeguard and as a fisherman. But while he surfed in Mission Beach he became friends with two other surfing pioneers, Dorian “Doc” Paskowitz and Bill “Hadji” Hein.

Paskowitz now lives in Waikiki Beach, overlooking the Koolau Range. Over the phone, he spoke to Surfshot about those pioneer days.

“I thought I was the first surfer in San Diego,” says Paskowitz, 83 and founder of the Paskowitz Surf Camp. “When I got to Mission Beach in 1934, I didn’t see any other surfers. I was so bummed.”

Paskowitz was one of the first surfers in Galveston, Texas. (He would later introduce the sport of surfing to Israel in the 1950s.) He claims to have walked from PB to OB on a quest to see one person with a surfboard.

“I couldn’t believe it,” he says. “There were more surfers in Texas than there were in San Diego. Emil and Charlie’s boards had vanished and Emil wasn’t surfing anymore by the time I got to San Diego. ”

Eventually Paskowitz heard of Charlie Wright and tracked him down. Wright gave Paskowitz his 90-pound mud-filled board.

“If you want a real hairy experience,” says Paskowitz, try taking a solid redwood 100 pound surfboard and take it out in the shorebreak in Mission Beach. I used that board for all of 1934 and ’35.

In 1938, Paskowitz got a custom made balsa board. “Boy was it gorgeous,” he remembers. ” It was 50 pounds, 11 ’6″, redwood nose and tail block with a balsa stringer.”

Woody Brown was one of Paskowitz’s surfing buddies. Brown is in his early 90s and also lives in Hawaii but was unavailable for this feature.

“Woody would go out in 30 foot waves,” recalls Paskowitz, who keeps in touch with Brown. “But not me; my limit was 15 foot, whether it was Makaha or the North Shore.”

If you surf Blacks Beach and appreciate the glider port above it, you can thank Brown. He single-handedly prevented what is now the Torrey Pines Glider Port from being commercially developed.

Brown, who befriended Charles Lindbergh before his historic trans-Atlantic flight in 1927, set several records for non-mechanized glider flying. Brown was one of the first surfers in La Jolla, having surfed there from 1935-9. As reported by Malcolm Williams on legendarysurfers.com, Brown, using his expert glider construction techniques, built his first surfboard out of plywood, which was hollow, 9’4″ and 22 inches wide.

The New York native was soon joined at Bird Rock and Windansea by Towny Cromwell and Don Okey (who passed away this past November and was the person primarily responsible for building the first surf shack in San Diego County).

Brown eventually moved to Hawaii after becoming despondent over the unexpected death of his wife. But before he moved, he was one of the first surfers here who experimented with hollow boards, which were still made of a plywood box. The major change in Brown’s board was that it had a skeg (fin) on it, which made him one of the first surfers in San Diego to surf with one.

It wasn’t until a decade after Brown and one of the first believed to have put a skeg on a board-Tom Blake-that surfers started using fins en mass. After settling in Hawaii, Brown was one of the first to surf the north shore of Oahu.

Judd

Judd Handler is a freelance writer and wellness/lifestyle coach in Encinitas, California. He surfs uncrowded, fun reef breaks; plays instrumental alternate-tuning guitar; goes hiking in the backcountry; and is amazed on a daily basis by just being alive.